Catalytic Staudinger/Aza??Wittig Sequence by in situ Phosphane Oxide Reduction

HA van Kalkeren, C te Grotenhuis…

Index: Van Kalkeren, Henri A.; Te Grotenhuis, Colet; Haasjes, Frank S.; Hommersom; Rutjes, Floris P. J. T.; Van Delft, Floris L. European Journal of Organic Chemistry, 2013 , # 31 p. 7059 - 7066

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Citation Number: 10

Abstract

Abstract A Staudinger/aza-Wittig reaction sequence is described that is catalytic in phosphorus. Towards this end, the phosphane oxide is reduced in situ by diphenylsilane, which allows for substoichiometric amounts of the catalyst 5-phenyldibenzophosphole to be used. The substrate scope is investigated and benzoxazoles, benzodiazepine imidates and a 2-methoxypyrrole were successfully synthesized. These investigations show that a fast ...